Methyleugenol (BioDeep_00000008098)

 

Secondary id: BioDeep_00000859463

human metabolite PANOMIX_OTCML-2023 Endogenous Volatile Flavor Compounds


代谢物信息卡片


METHYLEUGENOL (CONSTITUENT OF HOLY BASIL LEAF) [DSC]

化学式: C11H14O2 (178.09937440000002)
中文名称: 甲基丁香酚, 丁香酚甲醚, 甲基丁子香酚
谱图信息: 最多检出来源 Viridiplantae(plant) 0.06%

分子结构信息

SMILES: c1(c(ccc(c1)CC=C)OC)OC
InChI: InChI=1S/C11H14O2/c1-4-5-9-6-7-10(12-2)11(8-9)13-3/h4,6-8H,1,5H2,2-3H3

描述信息

Methyleugenol, also known as 4-allylveratrole or eugenol methyl, belongs to the class of organic compounds known as dimethoxybenzenes. These are organic aromatic compounds containing a monocyclic benzene moiety carrying exactly two methoxy groups. FDA noted the action was despite its continuing stance that this substance does not pose a risk to public health under the conditions of its intended use. Methyleugenol is a sweet, anise, and apricot tasting compound. Methyleugenol is found, on average, in the highest concentration within a few different foods, such as allspices, tarragons, and sweet bay and in a lower concentration in sweet basils, rosemaries, and hyssops. Methyleugenol has also been detected, but not quantified, in several different foods, such as soy beans, evergreen blackberries, muskmelons, citrus, and pomes. This could make methyleugenol a potential biomarker for the consumption of these foods. As of October 2018, the US FDA withdrew authorization for the use of methyl eugenol as a synthetic flavoring substance for use in food because petitioners provided data demonstrating that these additives induce cancer in laboratory animals. Methyleugenol is formally rated as a possible carcinogen (by IARC 2B) and is also a potentially toxic compound. Methyl eugenol (allylveratrol) is a natural chemical compound classified as a phenylpropene, a type of phenylpropanoid. It is the methyl ether of eugenol and is important to insect behavior and pollination. Their ability to attract insects, particularly Bactrocera fruit flies was first noticed in 1915 by F. M. Howlett. The compound may have evolved in response to pathogens, as methyl eugenol has some antifungal activity. Methyl eugenol is found in a number of plants (over 450 species from 80 families including both angiosperm and gymnosperm families) and has a role in attracting pollinators. About 350 plant species have them as a component of floral fragrance.
Methyleugenol is a clear colorless to pale yellow liquid with a spicy earthy odor. Bitter burning taste. (NTP, 1992)
O-methyleugenol is a phenylpropanoid. It is functionally related to a eugenol.
Methyleugenol is a natural product found in Vitis rotundifolia, Elettaria cardamomum, and other organisms with data available.
Methyleugenol is a yellowish, oily, naturally occurring liquid with a clove-like aroma and is present in many essential oils. Methyleugenol is used as a flavoring agent, as a fragrance and as an anesthetic in rodents. Methyleugenol is mutagenic in animals and is reasonably anticipated to be a human carcinogen based on evidence of carcinogenicity in animals. (NCI05)
Methyleugenol is found in allspice. Methyleugenol is present in many essential oils, e.g. nutmeg, mace and also many fruits, e.g. apple, banana, orange juice or peel, grapefruit, bilberryMethyleugenol has been shown to exhibit anti-nociceptive function (A7914).Methyleugenol belongs to the family of Anisoles. These are organic compounds contaiing a methoxybenzene or a derivative thereof.
Present in many essential oils, e.g. nutmeg, mace and also many fruits, e.g. apple, banana, orange juice or peel, grapefruit, bilberry. Methyleugenol is found in many foods, some of which are wild carrot, sweet basil, citrus, and fruits.
D002491 - Central Nervous System Agents > D002492 - Central Nervous System Depressants > D000777 - Anesthetics
D009676 - Noxae > D002273 - Carcinogens
D009676 - Noxae > D009153 - Mutagens
Methyl Eugenol, a phenylpropanoid chemical in leaves, fruits, stems, and/or roots, may be released when that corresponding part of a plant is damaged as a result of feeding by an herbivore. Methyl Eugenol is used for male annihilation of the oriental fruit fly[1].
Methyl Eugenol is a bait that has oral activity against oriental fruit fly (Hendel).Methyl Eugenol has anti-cancer and anti-inflammatory activities. Methyl Eugenol can induce Autophagy in cells. Methyl Eugenol can be used in the study of intestinal ischemia/reperfusion injury[1][2][3].
Methyl Eugenol, a phenylpropanoid chemical in leaves, fruits, stems, and/or roots, may be released when that corresponding part of a plant is damaged as a result of feeding by an herbivore. Methyl Eugenol is used for male annihilation of the oriental fruit fly[1].

同义名列表

68 个代谢物同义名

METHYLEUGENOL (CONSTITUENT OF HOLY BASIL LEAF) [DSC]; Benzene, 1,2-dimethoxy-4-(2-propen-1-yl)-; 1,2-dimethoxy-4-(prop-2-en-1-yl)benzene; Benzene, 1,2-dimethoxy-4-(2-propenyl)-; 1,2-Dimethoxy-4-(2-propen-1-yl)benzene; Benzene, 4-(2-propenyl)-1,2-dimethoxy; 1, 2-Dimethoxy-4-(2-propenyl)benzene; Dimethoxy-4-(prop-2-en-1-yl)benzene; Benzene,2-dimethoxy-4-(2-propenyl)-; 1,2-Dimethoxy-4-(2-propenyl)benzene; Methyl eugenol, analytical standard; 3,4-Dimethoxy-1-(2-propenyl)benzene; 1,2-dimethoxy-4-prop-2-enylbenzene; 1-(3, 4-Dimethoxyphenyl)-2-propene; 4-Allyl-1,2-dimethoxybenzene, 99\\%; 1-(3,4-Dimethoxyphenyl)-2-propene; 3-(3,4-dimethoxyphenyl)-1-propene; Benzene, 4-allyl-1,2-dimethoxy-; 3-(3,4-Dimethoxyphenyl)propene; 1,2-Dimethoxy-4-allyl benzene; 4-Allyl-1, 2-dimethoxybenzene; 4-Allyl-1,2-dimethyoxybenzene; 4-allyl-1,2-dimethoxy-benzene; 1,2-Dimethoxy-4-allylbenzene; 1-allyl-3,4-dimethoxybenzene; 4-allyl-1,2-dimethoxybenzene; EUGENYL METHYL ETHER [FHFI]; Methyl eugenol, >=98\\%, FCC; Allyl-1,2-dimethoxybenzene; 1,3,4-Eugenol methyl ether; 3,4-Dimethoxyallylbenzene; TRIDEUTEROMETHYL EUGENOL; 1,4-Eugenol methyl ether; CHAVIBETOL METHYL ETHER; o-Methyl eugenol ether; Veratrole methyl ether; METHYL EUGENOL [INCI]; Eugenyl methyl ether; Methyl eugenol ether; Methyl eugenyl ether; eugenol methyl ether; methyl ester eugenol; Eugenol-methyl ether; METHYL EUGENOL [FCC]; METHYLEUGENOL [IARC]; METHYLEUGENOL [HSDB]; VERATROLE, 4-ALLYL-; METHYLEUGENOL [MI]; Methyleugenol,(S); WLN: 1U2R CO1 DO1; 4-Allylveratrole; METHYLCHAVIBETOL; O-Methyl eugenol; UNII-29T9VA6R7M; O-Methyleugenol; methyl eugenol; Eugenol methyl; Allylveratrol; Methyleugenol; Tox21_300071; Tox21_202347; CAS-93-15-2; 29T9VA6R7M; FEMA 2475; AI3-21040; Methyl; Methyleugenol; Methyleugenol



数据库引用编号

25 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(2)

BioCyc(1)

PlantCyc(1)

代谢反应

32 个相关的代谢反应过程信息。

Reactome(2)

  • Olfactory Signaling Pathway: GTP + odorant:Olfactory Receptor:GNAL:GDP:GNB1:GNG13 ⟶ GDP + odorant:Olfactory Receptor:GNAL:GTP:GNB1:GNG13
  • Sensory Perception: GTP + odorant:Olfactory Receptor:GNAL:GDP:GNB1:GNG13 ⟶ GDP + odorant:Olfactory Receptor:GNAL:GTP:GNB1:GNG13

BioCyc(1)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(29)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

187 个相关的物种来源信息

在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有：

  • PubMed: 来源于PubMed文献库中的文献信息，我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表，这个列表按照代谢物同时出现的文献数量降序排序，取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
  • NCBI Taxonomy: 通过文献数据挖掘，得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序，取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
  • Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
  • Chemical Reaction: 在化学反应过程中，存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。

点击图上的相关代谢物的名称，可以跳转到相关代谢物的信息页面。



文献列表

  • Chao Yang, Yongsheng Lin, Xuwen Xiang, Dandan Shao, Ziwen Qiu, Yongyu Li, Shaohua Wu. MbEOMT1 regulates methyleugenol biosynthesis in Melaleuca bracteata F. Muell. Tree physiology. 2024 Apr; 44(4):. doi: 10.1093/treephys/tpae034. [PMID: 38498320]
  • Raju Balaji, Madasamy Parani. Development of an allele-specific PCR (AS-PCR) method for identifying high-methyl eugenol-containing purple Tulsi (Ocimum tenuiflorum L.) in market samples. Molecular biology reports. 2024 Mar; 51(1):439. doi: 10.1007/s11033-024-09365-0. [PMID: 38520476]
  • Alexandre Rolim Mineto, Sheila Porto de Matos, Isabella Morel Bordignon, Rayssa Ribeiro, Miriam Anders Apel, Valdir Florêncio da Veiga-Junior, Letícia Scherer Koester. Development by design of experiment and validation of a HPLC-UV method for simultaneous quantification of 1-nitro-2-phenylethane and methyleugenol: Application to nail permeation/retention studies. Journal of pharmaceutical and biomedical analysis. 2024 Feb; 239(?):115889. doi: 10.1016/j.jpba.2023.115889. [PMID: 38056286]
  • Thomas Fezza, Todd E Shelly, Abbie Fox, Kyle Beucke, Eric Rohrig, Charlotte Aldebron, Nicholas C Manoukis. Less is more: Fewer attract-and-kill sites improve the male annihilation technique against Bactrocera dorsalis (Diptera: Tephritidae). PloS one. 2024; 19(3):e0300866. doi: 10.1371/journal.pone.0300866. [PMID: 38512951]
  • Ellen de Nazaré S da Cruz, Luana de Sousa P Barros, Bruna de A Guimarães, Rosa Helena V Mourão, José Guilherme S Maia, William N Setzer, Joyce Kelly do R da Silva, Pablo Luis B Figueiredo. Seasonal Variation in Essential Oil Composition and Antioxidant Capacity of Aniba canelilla (Lauraceae): A Reliable Source of 1-Nitro-2-phenylethane. Molecules (Basel, Switzerland). 2023 Nov; 28(22):. doi: 10.3390/molecules28227573. [PMID: 38005295]
  • Awais Rasool, Sehar Fatima, Said Hussain Shah, Muhammad Farooq Hussain Munis, Afshan Irshad, Todd E Shelly, Ihsan Ul Haq. Methyl eugenol aromatherapy: a delivery system facilitating the simultaneous application of male annihilation and sterile insect technique against the peach fruit fly. Pest management science. 2023 Nov; ?(?):. doi: 10.1002/ps.7877. [PMID: 37941165]
  • Kai Nieschalke, Nick Bergau, Sönke Jessel, Albrecht Seidel, Susanne Baldermann, Monika Schreiner, Klaus Abraham, Alfonso Lampen, Bernhard H Monien, Burkhard Kleuser, Hansruedi Glatt, Fabian Schumacher. Urinary Excretion of Mercapturic Acids of the Rodent Carcinogen Methyleugenol after a Single Meal of Basil Pesto: A Controlled Exposure Study in Humans. Chemical research in toxicology. 2023 Oct; ?(?):. doi: 10.1021/acs.chemrestox.3c00212. [PMID: 37875262]
  • Probir Kumar Ghosh, Dipshikha Tamili, Anamika Das, Sanjukta Datta, Satadal Das, Subhankar Saha, Ketousetuo Kuotsu, Paramita Bhattacharjee. Valorization of tuberose flower waste through development of therapeutic products using supercritical carbon dioxide extraction and microencapsulation technologies. World journal of microbiology & biotechnology. 2023 Sep; 39(11):319. doi: 10.1007/s11274-023-03761-7. [PMID: 37743395]
  • Adam Yasgar, Danielle Bougie, Richard T Eastman, Ruili Huang, Misha Itkin, Jennifer Kouznetsova, Caitlin Lynch, Crystal McKnight, Mitch Miller, Deborah K Ngan, Tyler Peryea, Pranav Shah, Paul Shinn, Menghang Xia, Xin Xu, Alexey V Zakharov, Anton Simeonov. Quantitative Bioactivity Signatures of Dietary Supplements and Natural Products. ACS pharmacology & translational science. 2023 May; 6(5):683-701. doi: 10.1021/acsptsci.2c00194. [PMID: 37200814]
  • Fawang Liu, Tahir Ali, Zhong Liu. Molecular cloning and characterization of Cinnamoyl-CoA reductase promoter gene from Asarum sieboldii Miq. Biotechnology and applied biochemistry. 2023 Feb; 70(1):83-96. doi: 10.1002/bab.2330. [PMID: 35244949]
  • Xiujuan Pan, He Xiao, Xinping Hu, Zhi Long Liu. Insecticidal activities of the essential oil of Rhynchanthus beesianus rhizomes and its constituents against two species of grain storage insects. Zeitschrift fur Naturforschung. C, Journal of biosciences. 2023 Jan; 78(1-2):83-89. doi: 10.1515/znc-2022-0017. [PMID: 36130869]
  • Xiaoling Zhang, Susan P Felter, Anne Marie Api, Kaushal Joshi, Dan Selechnik. A Cautionary tale for using read-across for cancer hazard classification: Case study of isoeugenol and methyl eugenol. Regulatory toxicology and pharmacology : RTP. 2022 Dec; 136(?):105280. doi: 10.1016/j.yrtph.2022.105280. [PMID: 36367523]
  • Max J Carlsson, Anastasia S Vollmer, Philipp Demuth, Daniel Heylmann, Diana Reich, Caroline Quarz, Birgit Rasenberger, Teodora Nikolova, Thomas G Hofmann, Markus Christmann, Julia A Fuhlbrueck, Simone Stegmüller, Elke Richling, Alexander T Cartus, Jörg Fahrer. p53 triggers mitochondrial apoptosis following DNA damage-dependent replication stress by the hepatotoxin methyleugenol. Cell death & disease. 2022 11; 13(11):1009. doi: 10.1038/s41419-022-05446-9. [PMID: 36446765]
  • Zhao Liu, Qian-Ping Xie, Huai-Wang Guo, Wei Xu, Jin-Jun Wang. An odorant binding protein mediates Bactrocera dorsalis olfactory sensitivity to host plant volatiles and male attractant compounds. International journal of biological macromolecules. 2022 Oct; 219(?):538-544. doi: 10.1016/j.ijbiomac.2022.07.198. [PMID: 35907466]
  • R A I Drew, D L Hancock. Biogeography, Speciation and Taxonomy within the genus Bactrocera Macquart with application to the Bactrocera dorsalis (Hendel) complex of fruit flies (Diptera: Tephritidae: Dacinae). Zootaxa. 2022 Sep; 5190(3):333-360. doi: 10.11646/zootaxa.5190.3.2. [PMID: 37045165]
  • Xiaofeng Chen, Hui Yang, Shuangxiong Wu, Wei Zhao, Gefei Hao, JinJun Wang, Hongbo Jiang. BdorOBP69a is involved in the perception of the phenylpropanoid compound methyl eugenol in oriental fruit fly (Bactrocera dorsalis) males. Insect biochemistry and molecular biology. 2022 08; 147(?):103801. doi: 10.1016/j.ibmb.2022.103801. [PMID: 35717009]
  • Bai-Cheng Kuang, Shuai-Heng Hou, G Ji Zhan, Meng-Qin Wang, Jia-Si Zhang, Kai-Lun Sun, Zhi-Heng Wang, Qing-Wen Li, Nian-Qiao Gong. [Effect of methyl eugenol on hypoxia/reoxygenation injury of human renal tubular epithelial cells and its mechanism]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2021 Dec; 46(24):6502-6510. doi: 10.19540/j.cnki.cjcmm.20210918.402. [PMID: 34994143]
  • Xiaofeng Chen, Yibo Lei, Hongfei Li, Li Xu, Hui Yang, Jinjun Wang, Hongbo Jiang. CRISPR/Cas9 mutagenesis abolishes odorant-binding protein BdorOBP56f-2 and impairs the perception of methyl eugenol in Bactrocera dorsalis (Hendel). Insect biochemistry and molecular biology. 2021 12; 139(?):103656. doi: 10.1016/j.ibmb.2021.103656. [PMID: 34582991]
  • Fawang Liu, Tahir Ali, Zhong Liu. Comparative Transcriptomic Analysis Reveals the Effects of Drought on the Biosynthesis of Methyleugenol in Asarum sieboldii Miq. Biomolecules. 2021 08; 11(8):. doi: 10.3390/biom11081233. [PMID: 34439899]
  • Eduardo Valarezo, Vladimir Morocho, Luis Cartuche, Fernanda Chamba-Granda, Magdaly Correa-Conza, Ximena Jaramillo-Fierro, Miguel Angel Meneses. Variability of the Chemical Composition and Bioactivity between the Essential Oils Isolated from Male and Female Specimens of Hedyosmum racemosum (Ruiz & Pav.) G. Don. Molecules (Basel, Switzerland). 2021 Jul; 26(15):. doi: 10.3390/molecules26154613. [PMID: 34361766]
  • Seon-Mi Seo, Jae-Woo Lee, Jonghyun Shin, Jun-Hyung Tak, Jinho Hyun, Il-Kwon Park. Development of cellulose nanocrystal-stabilized Pickering emulsions of massoia and nutmeg essential oils for the control of Aedes albopictus. Scientific reports. 2021 06; 11(1):12038. doi: 10.1038/s41598-021-91442-6. [PMID: 34103581]
  • Nikolaos Nenadis, Maria Papapostolou, Maria Z Tsimidou. Suggestions on the Contribution of Methyl Eugenol and Eugenol to Bay Laurel (Laurus nobilis L.) Essential Oil Preservative Activity through Radical Scavenging. Molecules (Basel, Switzerland). 2021 Apr; 26(8):. doi: 10.3390/molecules26082342. [PMID: 33920599]
  • Yuqi Fan, Dongyue Yang, Xuhua Huang, Guangzhe Yao, Wei Wang, Mengyuan Gao, Xiaohua Jia, Huizi Ouyang, Yanxu Chang, Jun He. Pharmacokinetic Study of Safrole and Methyl Eugenol after Oral Administration of the Essential Oil Extracts of Asarum in Rats by GC-MS. BioMed research international. 2021; 2021(?):6699033. doi: 10.1155/2021/6699033. [PMID: 33829063]
  • Héctor Isaac Rocha-González, María Elena Sánchez-Mendoza, Leticia Cruz-Antonio, Francisco Javier Flores-Murrieta, Xochilt Itzel Cornelio-Huerta, Jesús Arrieta. Antinociceptive Interaction and Pharmacokinetics of the Combination Treatments of Methyleugenol Plus Diclofenac or Ketorolac. Molecules (Basel, Switzerland). 2020 Nov; 25(21):. doi: 10.3390/molecules25215106. [PMID: 33153182]
  • Kai-Fei Guo, Man Dai, Yi-Miao Liu, Ji-Chuan Zhang, Yan-Mei Chen, Hui Ye, Man-Bi Li, Rong-Rong Mao, Jun Cao. Acute Administration of Methyleugenol Impairs Hippocampus-Dependent Contextual Fear Memory and Increases Anxiety-like Behavior in Mice. Journal of agricultural and food chemistry. 2020 Jul; 68(28):7490-7497. doi: 10.1021/acs.jafc.0c01863. [PMID: 32551566]
  • K-H Tan. Recaptures of feral Bactrocera dorsalis and B. umbrosa (Diptera: Tephritidae) males after feeding on methyl eugenol. Bulletin of entomological research. 2020 Feb; 110(1):15-21. doi: 10.1017/s0007485319000208. [PMID: 31190651]
  • Roktim Gogoi, Rikraj Loying, Neelav Sarma, Twahira Begum, Sudin K Pandey, Mohan Lal. Comparative Analysis of In-Vitro Biological Activities of Methyl Eugenol Rich Cymbopogon khasianus Hack., Leaf Essential Oil with Pure Methyl Eugenol Compound. Current pharmaceutical biotechnology. 2020; 21(10):927-938. doi: 10.2174/1389201021666200217113921. [PMID: 32065101]
  • Mosaab Yahyaa, Anna Berim, Bhagwat Nawade, Muhammad Ibdah, Natalia Dudareva, Mwafaq Ibdah. Biosynthesis of methyleugenol and methylisoeugenol in Daucus carota leaves: Characterization of eugenol/isoeugenol synthase and O-Methyltransferase. Phytochemistry. 2019 Mar; 159(?):179-189. doi: 10.1016/j.phytochem.2018.12.020. [PMID: 30634080]
  • Po-Hung Chen, Wen-Jer Wu, Ju-Chun Hsu. Detection of Male Oriental Fruit Fly (Diptera: Tephritidae) Susceptibility to Naled- and Fipronil-Intoxicated Methyl Eugenol. Journal of economic entomology. 2019 02; 112(1):316-323. doi: 10.1093/jee/toy278. [PMID: 30260395]
  • Jinjie Liu, Chong Xu, Honglei Zhang, Fawang Liu, Dongming Ma, Zhong Liu. Comparative Transcriptomics Analysis for Gene Mining and Identification of a Cinnamyl Alcohol Dehydrogenase Involved in Methyleugenol Biosynthesis from Asarum sieboldii Miq. Molecules (Basel, Switzerland). 2018 Dec; 23(12):. doi: 10.3390/molecules23123184. [PMID: 30513938]
  • Edenilson Dos Santos Niculau, Leandro do Prado Ribeiro, Thiago Felipe Ansante, João Batista Fernandes, Moacir Rossi Forim, Paulo Cezar Vieira, José Djair Vendramim, Maria Fátima das Graças Fernandes da Silva. Isolation of Chavibetol and Methyleugenol from Essential Oil of Pimenta pseudocaryophyllus by High Performance Liquid Chromatography. Molecules (Basel, Switzerland). 2018 Nov; 23(11):. doi: 10.3390/molecules23112909. [PMID: 30413007]
  • Tainá Kreutz, Letícia G Lucca, Orlando A R Loureiro-Paes, Helder F Teixeira, Valdir F Veiga, Renata P Limberger, George G Ortega, Letícia S Koester. Optimization, validation and application of headspace solid-phase microextraction gas chromatography for the determination of 1-nitro-2-phenylethane and methyleugenol from Aniba canelilla (H.B.K.) Mez essential oil in skin permeation samples. Journal of chromatography. A. 2018 Aug; 1564(?):163-175. doi: 10.1016/j.chroma.2018.05.073. [PMID: 29910087]
  • Scott S Auerbach, Miaofei Xu, B Alex Merrick, Mark J Hoenerhoff, Dhiral Phadke, Debra J Taxman, Ruchir Shah, Hue-Hua L Hong, Thai-Vu Ton, Ramesh C Kovi, Robert C Sills, Arun R Pandiri. Exome Sequencing of Fresh-frozen or Formalin-fixed Paraffin-embedded B6C3F1/N Mouse Hepatocellular Carcinomas Arising Either Spontaneously or due to Chronic Chemical Exposure. Toxicologic pathology. 2018 08; 46(6):706-718. doi: 10.1177/0192623318789398. [PMID: 30045675]
  • Li Yin, Zhaohui Sun, Qian Ren, Xian Su, Delong Zhang. Methyl eugenol induces potent anticancer effects in RB355 human retinoblastoma cells by inducing autophagy, cell cycle arrest and inhibition of PI3K/mTOR/Akt signalling pathway. Journal of B.U.ON. : official journal of the Balkan Union of Oncology. 2018 Jul; 23(4):1174-1178. doi: . [PMID: 30358228]
  • Sarmistha Saha, Ramtej J Verma. Molecular interactions of active constituents of essential oils in zwitterionic lipid bilayers. Chemistry and physics of lipids. 2018 07; 213(?):76-87. doi: 10.1016/j.chemphyslip.2018.03.008. [PMID: 29596800]
  • Ihsan Ul Haq, Carlos Cáceres, José S Meza, Jorge Hendrichs, Marc J B Vreysen. Different methods of methyl eugenol application enhance the mating success of male Oriental fruit fly (Dipera: Tephritidae). Scientific reports. 2018 04; 8(1):6033. doi: 10.1038/s41598-018-24518-5. [PMID: 29662085]
  • Yukun Feng, Saide Wang, Hui Wang, Ying Peng, Jiang Zheng. Urinary Methyleugenol-deoxyadenosine Adduct as a Potential Biomarker of Methyleugenol Exposure in Rats. Journal of agricultural and food chemistry. 2018 Feb; 66(5):1258-1263. doi: 10.1021/acs.jafc.7b05186. [PMID: 29328669]
  • Huan Liu, Xiao-Feng Zhao, Lang Fu, Yi-Ye Han, Jin Chen, Yong-Yue Lu. BdorOBP2 plays an indispensable role in the perception of methyl eugenol by mature males of Bactrocera dorsalis (Hendel). Scientific reports. 2017 Nov; 7(1):15894. doi: 10.1038/s41598-017-15893-6. [PMID: 29162858]
  • Fatemeh Khakdan, Jaber Nasiri, Mojtaba Ranjbar, Houshang Alizadeh. Water deficit stress fluctuates expression profiles of 4Cl, C3H, COMT, CVOMT and EOMT genes involved in the biosynthetic pathway of volatile phenylpropanoids alongside accumulation of methylchavicol and methyleugenol in different Iranian cultivars of basil. Journal of plant physiology. 2017 Nov; 218(?):74-83. doi: 10.1016/j.jplph.2017.07.012. [PMID: 28787649]
  • Mervyn Shepherd, Dale Savins, Ashley Dowell, Samantha Morrow, Gareth Allen, Ian Southwell. Ecotype Variation of Methyl Eugenol Content in Tea Tree (Melaleuca alternifolia and Melaleuca linariifolia). Chemistry & biodiversity. 2017 Nov; 14(11):. doi: 10.1002/cbdv.201700278. [PMID: 28749029]
  • Hanan Saleh, Haidan M El-Shorbagy. Mechanism underlying methyl eugenol attenuation of intestinal ischemia/reperfusion injury. Applied physiology, nutrition, and metabolism = Physiologie appliquee, nutrition et metabolisme. 2017 Oct; 42(10):1097-1105. doi: 10.1139/apnm-2017-0043. [PMID: 28651060]
  • Andrea Muráriková, Anton Ťažký, Jarmila Neugebauerová, Alexandra Planková, Josef Jampílek, Pavel Mučaji, Peter Mikuš. Characterization of Essential Oil Composition in Different Basil Species and Pot Cultures by a GC-MS Method. Molecules (Basel, Switzerland). 2017 Jul; 22(7):. doi: 10.3390/molecules22071221. [PMID: 28726757]
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